2-bromo-3,5-bis(methoxymethoxy)benzaldehyde | 620177-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-bromo-3,5-bis(methoxymethoxy)benzaldehyde
• CAS: 620177-96-0
• 化学式: C₁₁H₁₃BrO₅
• 分子量: 305.125
• InChiKey: XCOVHDYVLSZDMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-bromo-3,5-bis(methoxymethoxy)benzaldehyde 在 tris(dibenzylideneacetone)dipalladium (0) 甲醇 、 正丁基锂 、 三叔丁基膦 、 camphor-10-sulfonic acid 、 戴斯-马丁氧化剂 、 cesium fluoride 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 反应 47.25h， 生成 [3,5-dihydroxy-2-(3-methylbut-2-enyl)phenyl](3,5-dichloro-2-hydroxy-6-methoxy-4-methylphenyl)methanone
  参考文献：
  名称：

  Synthetic analogues of the antibiotic pestalone

  摘要：

  The first synthetic study towards the natural product pestalone (1) is described culminating in the preparation of selected n-1 analogues. Pestalone is a chlorinated and prenylated benzophenone antibiotic, which is of interest due to a strong activity against methicillin-resistant staphylococcus aureus strains (MRSA). Key step of the synthesis is the nucleophilic addition of a highly functionalized aryllithium building block to a 2-prenylated 3,5-dialkoxy-benzaldehyde followed by oxidation. For the introduction of the prenyl sidechain by aryl-allyl coupling, different procedures were evaluated, among them the Stille reaction and a nickel pi-allyl complex coupling. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01136-0
• 作为产物：
  描述：

  (2-bromo-3,5-bis(methoxymethoxy)phenyl)methanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 2-bromo-3,5-bis(methoxymethoxy)benzaldehyde
  参考文献：
  名称：

  Su, Ying; Ma, Junying; Peng, Xuanjia, Journal of Chemical Research, 2004, # 10, p. 704 - 705

  摘要：

  DOI：

文献信息

• Total Synthesis of Dendrochrysanene through a Frame Rearrangement
  作者：Naoki Katsuki、Shumpei Isshiki、Daisuke Fukatsu、Juan Okamura、Kouji Kuramochi、Takeo Kawabata、Kazunori Tsubaki

  DOI：10.1021/acs.joc.7b02223

  日期：2017.11.3

  for the rearrangement reaction; however, at such temperatures, the substrate decomposed. To address this issue, we added phenylethylamine or benzylamine to the reaction system. We assumed that the amine trapped generated hydrochloric acid and acted as a ligand for iron, helping to maintain an appropriate redox potential. The total synthesis of dendrochrysanene, involving this rearrangement reaction

  首次实现了全树突烯的全合成（1）。构建树烯三烯的关键反应是从菲二聚体到螺内酯骨架的氧化构架重排反应，我们偶然发现了该反应。由于取代基的对位阻迫菲二聚体的位置，重排反应需要高温条件；但是，在这样的温度下，基板分解。为了解决这个问题，我们在反应体系中加入了苯乙胺或苄胺。我们假设胺会捕获生成的盐酸并充当铁的配体，从而有助于保持适当的氧化还原电势。涉及该重排反应的树突丙烯烯的总合成是连接菲衍生物，菲二聚体和螺内酯化合物的重要序列，这些化合物通常从兰科植物中分离出来。
• Su, Ying; Ma, Junying; Peng, Xuanjia, Journal of Chemical Research, 2004, # 10, p. 704 - 705
  作者：Su, Ying、Ma, Junying、Peng, Xuanjia、She, Xuegong、Pan, Xinfu、Gao, Jinming

  DOI：——

  日期：——
• Synthetic analogues of the antibiotic pestalone
  作者：Florian Kaiser、Hans-Günther Schmalz

  DOI：10.1016/s0040-4020(03)01136-0

  日期：2003.9

  The first synthetic study towards the natural product pestalone (1) is described culminating in the preparation of selected n-1 analogues. Pestalone is a chlorinated and prenylated benzophenone antibiotic, which is of interest due to a strong activity against methicillin-resistant staphylococcus aureus strains (MRSA). Key step of the synthesis is the nucleophilic addition of a highly functionalized aryllithium building block to a 2-prenylated 3,5-dialkoxy-benzaldehyde followed by oxidation. For the introduction of the prenyl sidechain by aryl-allyl coupling, different procedures were evaluated, among them the Stille reaction and a nickel pi-allyl complex coupling. (C) 2003 Elsevier Ltd. All rights reserved.
• Enantioselective total synthesis of aigialomycin D
  作者：Jiangping Lu、Junying Ma、Xingang Xie、Bo Chen、Xuegong She、Xinfu Pan

  DOI：10.1016/j.tetasy.2006.03.027

  日期：2006.4

  An efficient, convergent approach for the total synthesis of aigialomycin D I is described. Key features of the synthetic strategy include (a) a Sharpless asymmetric epoxidation reaction and selective opening of a 2,3-epoxy alcohol to elaborate the two hydroxy-bearing stereogenic centers at the C5' and C6' positions; (b) a Kocienski modified Julia protocol to construct the two E-configured double bonds; and (c) Yamaguchi macrolactonization to acccess the 14-membered macrocyclic ring. (c) 2006 Elsevier Ltd. All rights reserved.